Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-FluoroacetophenoneNicola Pohl and Kimberly SchwarzDescribes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ.2008, 85, 834.

Aldehydes / Ketones |

NMR Spectroscopy |

Nucleophilic Substitution |

Synthesis

Acid-Catalyzed Enolization of β-TetraloneBrahmadeo Dewprashad, Anthony Nesturi, and Joel UrenaThis experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ.2008, 85, 829.

Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig ReactionEric Martin and Cynthia Kellen-YuenA microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ.2007, 84, 2004.

Hydration of Acetylene: A 125th AnniversaryDmitry A. Ponomarev and Sergey M. ShevchenkoThe discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ.2007, 84, 1725.

Addition Reactions |

Aldehydes / Ketones |

Alkynes |

Catalysis |

Industrial Chemistry |

Reactions

Lactate Dehydrogenase Catalysis: Roles of Keto, Hydrated, and Enol PyruvateJ. E. MeanyConsiders the reduction of pyruvate by lactate dehydrogenase in the presence of NADH. This reaction is inhibited by high concentrations of pyruvate, the physiological significance of which has long been controversial. This article summarizes the literature regarding the interactions of keto, hydrated, and enol pyruvate with lactate dehydrogenase. Meany, J. E. J. Chem. Educ.2007, 84, 1520.

Aldehydes / Ketones |

Bioenergetics |

Biophysical Chemistry |

Enzymes |

Equilibrium |

Mechanisms of Reactions |

Reactive Intermediates |

Thermodynamics

A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave ConditionsA. Gilbert CookThe product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.Cook, A. Gilbert. J. Chem. Educ.2007, 84, 1477.

Aldehydes / Ketones |

Conformational Analysis |

Gas Chromatography |

IR Spectroscopy |

Mass Spectrometry |

Mechanisms of Reactions |

NMR Spectroscopy |

Stereochemistry |

Synthesis

A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl CompoundsRobert E. RosenbergStudents teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones. Rosenberg, Robert E. J. Chem. Educ.2007, 84, 1474.

Oxidation of Aromatic Aldehydes Using OxoneRajani Gandhari, Padma P. Maddukuri, and Thottumkara K. VinodDescribes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ.2007, 84, 852.

Aldehydes / Ketones |

Aromatic Compounds |

Aqueous Solution Chemistry |

Carboxylic Acids |

Green Chemistry |

Mechanisms of Reactions |

NMR Spectroscopy |

Oxidation / Reduction

The GC–MS Observation of Intermediates in a Stepwise Grignard Addition ReactionDevin LatimerThis article describes a three-hour laboratory experiment for the third-year organic chemistry lab whereby the stable organic intermediates and final product of the Grignard addition of 3 equivalents of phenylmagnesium bromide to diethyl carbonate are observed.Latimer, Devin. J. Chem. Educ.2007, 84, 699.

Aldehydes / Ketones |

Grignard Reagents |

Synthesis |

Chromatography |

Instrumental Methods |

Mass Spectrometry |

Mechanisms of Reactions

Sudoku Puzzles for First-Year Organic Chemistry StudentsAlice L. Perez and G. LamoureuxSudoku puzzles are used to help the students learn the correspondence between the names of amino acids, their abbreviations, and codes; and the correspondence between the names of functional groups, their structures, and abbreviations.Perez, Alice L.; Lamoureux, G. J. Chem. Educ.2007, 84, 614.

The Aldol Addition and Condensation: The Effect of Conditions on Reaction PathwayR. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. BarkerDescribes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ.2007, 84, 475.

A Discovery-Learning 2,4-Dinitrophenylhydrazone ExperimentBruno M. Vittimberga and Ben RuekbergSelections of liquid aldehydes and ketones are proposed for students to determine what property is the best predictor of the color (yellow to red) of their 2,4-dinitrophenylhydrazone derivative. Students may use a computer (spreadsheet or word processor) to analyze their results.Vittimberga, Bruno M.; Ruekberg, Ben. J. Chem. Educ.2006, 83, 1661.

Aldehydes / Ketones |

Molecular Properties / Structure |

Physical Properties |

Qualitative Analysis

Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. BarkerDescribes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ.2006, 83, 1658.

Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry LaboratoryJacqueline Bennett, Kristen Meldi, and Christopher Kimmell IIIn this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) alpha-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.Bennett, Jacqueline; Meldi, Kristen; Kimmell, Christopher, II. J. Chem. Educ.2006, 83, 1221.

Octachem Model: Organic Chemistry Nomenclature CompanionJoaquin PalaciosThe Octachem model is an educational physical model designed to guide students in the identification, classification, and naming of the chemical structures of organic compounds. In this article the basic concepts of Octachem model are presented, and the physical model and contents are described.Palacios, Joaquin. J. Chem. Educ.2006, 83, 890.

Ozonolysis Problems That Promote Student ReasoningRay A. Gross Jr.The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.Gross, Ray A., Jr. J. Chem. Educ.2006, 83, 604.

Aldehydes / Ketones |

Alkenes |

Alkynes |

Carboxylic Acids |

Oxidation / Reduction |

Student-Centered Learning

Facing the Music: How Original Was Borodin's Chemistry?Michael D. GordinA return to the original sources demonstrates that the evidence for Borodin's reputation as a great chemist, as opposed to a merely good one, is exaggerated.Gordin, Michael D. J. Chem. Educ.2006, 83, 561.

Using Building-Block Puzzles To Practice Drawing Organic MechanismsEnder ErdikThis pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.Erdik, Ender. J. Chem. Educ.2005, 82, 1325.

Reactive Intermediates |

Synthesis |

Aldehydes / Ketones |

Mechanisms of Reactions

An Improved Preparation of 2,4-Dinitrophenylhydrazine ReagentBen Ruekberg and Eric RossoniIn the analysis of aldehydes and ketones (both for characterizing the functional group and identifying such compounds by the melting points of their derivatives), 2,4-dinitrophenylhydrazine reagent is often used. Of the several formulations of this reagent, the most popular uses sulfuric acid. The method involves making a paste of 2,4-dinitro-phenylhydrazine in concentrated sulfuric acid, dispersion of the paste in ethanol, addition of water, and the filtration of the reagent. This improvement uses milder conditions, which may obviate the need for the final filtration. Those responsible for preparation of stock reagent solutions for classes should note that this method facilitates scaling up the preparation.Ruekberg, Ben; Rossoni, Eric. J. Chem. Educ.2005, 82, 1310.

Aldehydes / Ketones |

Laboratory Equipment / Apparatus |

Laboratory Management

A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium BorohydrideLori L. White and Kevin W. KittredgeWe report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent. White, Lori L.; Kittredge, Kevin W. J. Chem. Educ.2005, 82, 1055.

Oxidation / Reduction |

Solid State Chemistry |

Green Chemistry |

Alcohols |

Aldehydes / Ketones

Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory ExperimentSam H. Leung and Stephen A. AngelIn this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.Leung, Sam H.; Angel, Stephen A. J. Chem. Educ.2004, 81, 1492.

Chromatography |

Green Chemistry |

Microscale Lab |

NMR Spectroscopy |

Synthesis |

Reactions |

Aldehydes / Ketones |

Alkenes

The Conversion of Carboxylic Acids to Ketones: A Repeated DiscoveryJohn W. Nicholson and Alan WilsonThis article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries. Nicholson, John W.; Wilson, Alan. J. Chem. Educ.2004, 81, 1362.

Conformational Analysis in an Advanced Integrated Laboratory CourseDavid B. Ball and Randy M. MillerAn interdisciplinary project is described that requires students to synthesize conformationally mobile and static a-bromocyclohexanones and to assess, qualitatively and quantitatively, and validate, using several spectroscopic tools, solvent effects on the conformational preferences of these molecules. The project exposes students to a variety of experimental and theoretical techniques that include organic synthesis, product purification, 1H and 13C NMR spectrometry, GCMS, molecular modeling, and IR and UV spectroscopy. Ball, David B.; Miller, Randy M. J. Chem. Educ.2004, 81, 121.

Organic Functional Group Playing Card DeckMichael J. WelshOrganic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.Welsh, Michael J. J. Chem. Educ.2003, 80, 426.

Synthesis and Spectroscopic Analysis of a Cyclic Acetal: A Dehydration Performed in Aqueous SolutionDavid M. Collard, Adolphus G. Jones, and Robert M. KriegelTreatment of pentaerythritol with benzaldehyde in aqueous acid to produce the monoacetal, 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane. The reaction has a number of interesting features: the isolated product is the monobenzal not the dibenzal, and the reaction, a dehydration, is performed in water. Collard, David M.; Jones, Adolphus G.; Kriegel, Robert M. J. Chem. Educ.2001, 78, 70.

NMR Spectroscopy |

Synthesis |

Aldehydes / Ketones |

Alcohols

Introducing Chiroscience into the Organic Laboratory CurriculumKenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ.2000, 77, 305.

Chirality / Optical Activity |

Chromatography |

Mechanisms of Reactions |

Synthesis |

Separation Science |

Stereochemistry |

Gas Chromatography |

Aldehydes / Ketones

Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic AcidSteven C. Cermak and David F. WiemerThe preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments.Cermak, Steven C.; Wiemer, David F. J. Chem. Educ.1999, 76, 1715.

Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic AldehydesN. Anoune, H. Hannachi, P. Lantéri, R. Longeray, and C. ArnaudThis is a project for advanced students in two parts. First: A study of the Baeyer-Villiger reaction on para-methoxybenzaldehyde. Such a reaction is commonly used to oxidize ketones into esters. Second: The experiment is extended to various polymethoxybenzaldehydes and theoretical calculations are used to explain their particular behaviors. Anoune, N.; Hannachi, H.; Lantéri, P.; Longeray, R.; Arnaud, Christian. J. Chem. Educ.1998, 75, 1290.

Mechanisms of Reactions |

Theoretical Chemistry |

Aldehydes / Ketones |

Aromatic Compounds

Synthesis of Aspirin: A General Chemistry ExperimentJohn A. Olmsted IIIAn experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.Olmsted, John A., III. J. Chem. Educ.1998, 75, 1261.

An Aldehyde DerivativeJ. Hodge Markgraf and Bo Yoon ChoiA system in which aldehydes are condensed with 1,2-benzenedimethylthiol in the presence of anhydrous ferric chloride on silica gel to give 3-substituted 1,5-dihyhdro-2,4-benzodithiepines. Melting points of the derivatives were taken as a means of identification of unknown compounds. Markgraf, J. Hodge; Choi, Bo Yoon. J. Chem. Educ.1998, 75, 222.

A -78°C Sequential Michael Addition for the Organic LabMichael W. TanisThis paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions. Tanis, Michael W. J. Chem. Educ.1997, 74, 112.

Following Microscale Organic Reactions Using FT-IREms-Wilson, JaniceThe progress of two microscale reactions, the reduction of cyclohexanone with sodium borohydride and the photochemical formation of benzopinacol, was monitored, qualitatively, using FT-IR.Ems-Wilson, Janice J. Chem. Educ.1996, 73, A171.

Microscale Lab |

Aldehydes / Ketones |

Photochemistry |

Oxidation / Reduction |

IR Spectroscopy

Following Microscale Organic Reactions Using FT-IRJanice Ems-WilsonThis article describes an experiment that encourages discussion of carbohydrate chemistry in terms of reaction mechanisms, conformational analysis, and spectroscopy. The specific experiment involves the preparation of the bis(acetonide) of D-(+)-mannose.Ems-Wilson, Janice. J. Chem. Educ.1996, 73, A170.

Microscale Lab |

Carbohydrates |

Mechanisms of Reactions |

Conformational Analysis |

Spectroscopy |

Synthesis |

Aldehydes / Ketones |

Alcohols

Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent SelectivityMichael G. Organ and Paul AndersonUndergraduate students leaving an organic chemistry program should have exposure to these concepts and hands-on experience in dealing practically with the issue of selectivity. In this paper, selective addition of a nucleophile to either end of the enone moiety in cyclohexenone is examined. Organ, Michael G.; Anderson, Paul. J. Chem. Educ.1996, 73, 1193.

Addition Reactions |

Aldehydes / Ketones |

Mechanisms of Reactions

An Organoleptic Laboratory ExperimentJohn M. RisleyCompounds in ten different classes of organic molecules that are used in the fragrance and food industry are provided to students. Students whiff the vapors of each compound and describe the organoleptic properties using a set of terms utilized in the fragrance and food industry. A set of questions guides students to an understanding of the relationship between structure of molecules and smell.Risley, John M. J. Chem. Educ.1996, 73, 1181.

Molecular Properties / Structure |

Consumer Chemistry |

Physical Properties |

Nonmajor Courses |

Alcohols |

Aldehydes / Ketones |

Amines / Ammonium Compounds |

Carboxylic Acids |

Esters |

Ethers |

Phenols

Mini-scale Oxidation/Reduction in Organic Laboratory Course: 4-Nitrobenzaldehyde/ 4-Nitrobenzyl AlcoholDouglass F. Taber, Yanong Wang, Sebastian LiehrOxidation of an alcohol to the aldehyde or ketone, and corresponding reduction back to the alcohol, are two of the most common transformations of preparative organic chemistry. We have found a much more satisfactory combination in 4-nitrobenzyl alcohol and 4-nitrobenzaldehyde: both are crystalline, neither is volatile, and both are strongly UV-absorbing, so they visualize well on TLC. Taber, Douglass F.; Wang, Yanong; Liehr, Sebastian. J. Chem. Educ.1996, 73, 1042.

The Mechanism of NaBH4 Addition to Aldehydes: A Labeling ExperimentRolland K. Robinson and Karl De JesusIn order to determine the sources of hydrogens in NaBH4 reductions of aldehydes, a series of reductions were carried out using differentially deuterated reagents and solvents. Robinson, Rolland K.; De Jesus, Karl. J. Chem. Educ.1996, 73, 264.

Revisiting Fehling and Discovering VogelBoll, Per M.Fehling's reagent, the story of copper(II) ions reaction with sugars, and the life and contributions of Heinrich August Vogel.Boll, Per M. J. Chem. Educ.1994, 71, 220.

A source of isomer-drawing assignmentsKjonaas, Richard A.A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.Kjonaas, Richard A. J. Chem. Educ.1992, 69, 452.

A novel ketone derivativeMelamedi, Dan; Pickering, MilesThe authors propose the use of thioketals as derivatives as a safer alternative that also illustrates an interesting but rarely visited corner of undergraduate organic chemistry.Melamedi, Dan; Pickering, Miles J. Chem. Educ.1991, 68, 1046.

The water solubility of 2-butanol: A widespread errorAlger, Donald B.There seems to be widespread misreporting of the solubility of 2-butanol. This misreporting is an example of the importance of consulting original sources.Alger, Donald B. J. Chem. Educ.1991, 68, 939.

A brief freshman experience in qualitative organic analysisGriswold, John R.; Rauner, Richard A.This is an experiment aimed at second semester non-major students. Because such courses attempt to cover so much material in so little time, laboratory experiences must be carefully thought out.Griswold, John R.; Rauner, Richard A. J. Chem. Educ.1991, 68, 418.

Nonmajor Courses |

Aldehydes / Ketones |

Alcohols |

Esters |

Phenols |

Qualitative Analysis

The synthesis of 2-methyl-4-heptanonede Jong, Elma A.; Feringa, Ben L.2-methyl-4-heptanone is an ant pheromone used to alarm fellow ants. The synthesis described in this article is greeted with interest by students.de Jong, Elma A.; Feringa, Ben L. J. Chem. Educ.1991, 68, 71.

Synthesis of a phenol-formaldehyde thermosetting polymerBedard, Y.; Riedl, B.Procedure that allows for the synthesis of a 50% aqueous solution of a prepolymer that, with the proper application of heat and pressure, can be used to bind together wood or other materials.Bedard, Y.; Riedl, B. J. Chem. Educ.1990, 67, 977.

A new look at carbonyl electronic transitionsHenderson, GilesIn this study the author has extended the use of superposition wave functions to describe the evolution of molecular orbitals in the carbonyl chomophore undergoing both p g p* and n g p* transitions.Henderson, Giles J. Chem. Educ.1990, 67, 392.

The subjection of glutaraldehyde to the Tollens testHill, William D., Jr.Redox equations have been established for the Tollens test with respect to compounds containing two aldehyde groups such as glutaraldehyde.Hill, William D., Jr. J. Chem. Educ.1990, 67, 329.

Disulfide interchange reactions: An enzymic case study Kitson, Trevor M.This article concerns the reaction known as "disulfide interchange" in which a thiol reacts with a disulfide to give a different thiol and disulfide pair as the products.Kitson, Trevor M. J. Chem. Educ.1988, 65, 829.

Aldehyde and ketone ligands in organometallic complexes and catalysis Huang, Yo Hsin; Gladysz, J. A.The purpose of this article is to acquaint the nonspecialist with an interface of organometallic chemistry and catalysis. In particular, what is the fundamental coordination chemistry of aldehydes and ketones?Huang, Yo Hsin; Gladysz, J. A. J. Chem. Educ.1988, 65, 298.

Aldehydes / Ketones |

Coordination Compounds |

Organometallics |

Molecular Properties / Structure |

NMR Spectroscopy

Organic lecture demonstrationsSilversmith, Ernest F.Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.Silversmith, Ernest F. J. Chem. Educ.1988, 65, 70.

Molecular Properties / Structure |

Nucleophilic Substitution |

Acids / Bases |

Physical Properties |

Alkenes |

Stereochemistry |

Enantiomers |

Chirality / Optical Activity |

Aldehydes / Ketones |

Alcohols

A modified Fehling test and a modified corrected Benedict testHill, William D, Jr.Reactions to demonstrate that iron(III) sulfate supplements copper(I) sulfate in the oxidation of aldehydes of any type (aliphatic, aromatic, a combination of the two, glutaraldehyde, and alpha-hydroxy) and alpha-hydroxy ketones.Hill, William D, Jr. J. Chem. Educ.1987, 64, 984.

Oxidation / Reduction |

Aldehydes / Ketones

A problem involving organic qualitative analysisSilvert, D. J.Five different organic compounds are to be identified from the result of three simple qualitative tests on each unknown (dichromate, DNPH, and iodoform tests).Silvert, D. J. J. Chem. Educ.1987, 64, 971.

A visual manifestation of the Norrish Type I reaction: The cyclohexanone sunburn dosimeterCarroll, Felix A.; Strouse, Geoffrey F.; Hain, Jon M.Irradiation of aqueous cyclohexanone solutions produces hex-5-enal and butylketene; the latter reacts with water to form caproic acid, which lowers the pH of the solution and thus can be used to measure the progress of the reaction.Carroll, Felix A.; Strouse, Geoffrey F.; Hain, Jon M. J. Chem. Educ.1987, 64, 84.

Prediction of the appearance of non-first-order proton NMR spectra Macomber, Roger S.Undergraduates generally become equipped only to handle only first-order coupling patterns. This means that they have a hard time understanding a real spectra. By scaffolding students through the synthesis level of Bloom's taxonomy, students can work toward a more expert level of understanding.Macomber, Roger S. J. Chem. Educ.1983, 60, 525.

NMR Spectroscopy |

Aldehydes / Ketones |

Learning Theories

A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetateLampman, Gary M.; Sharpe, Steven D.There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ.1983, 60, 503.

Ketone synthesis using household bleachPerkins, Robert A.; Chau, FelixHousehold bleach is used to synthesize several different ketones from alcohols.Perkins, Robert A.; Chau, Felix J. Chem. Educ.1982, 59, 981.

The principle of vinylogyKrishnamurthy, SubrahmanyaThe principle of vinylogy recognizes the possibility that the inductive effect of a functional group is transmitted through a double bond or a conjugated system of double bonds.Krishnamurthy, Subrahmanya J. Chem. Educ.1982, 59, 543.

Analysis of some synthetic reactions by the HSAB principleHo, Tse-LokThe specificity and efficiency of reactions often have been left unexplained. Addressing these deficiencies, we delineate an empirical analysis of a selected number of synthetic reactions based on the hard and soft acids and bases (HSAB) principle.Ho, Tse-Lok J. Chem. Educ.1978, 55, 355.

Acids / Bases |

Synthesis |

Aldehydes / Ketones |

Esters

Favorskii rearrangement in bridged polycyclic compoundsChenier, Philip J.Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.Chenier, Philip J. J. Chem. Educ.1978, 55, 286.

Mechanisms of Reactions |

Carboxylic Acids |

Aldehydes / Ketones |

Aromatic Compounds

Synthesis of furfuryl alcohol and furoic acidCarraher, Charles E., Jr.The exercise in this paper can be conducted utilizing two 3-hour laboratory periods and is meant to illustrate the 1) the use of the cannizzaro reaction in synthesis, 2) production of a commercial resin and 3) the importance of several natural products in the present industrial economy.Carraher, Charles E., Jr. J. Chem. Educ.1978, 55, 269.

The scope of the Haworth synthesisAgranat, Israel; Shih, Yu-ShanThe duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.Agranat, Israel; Shih, Yu-Shan J. Chem. Educ.1976, 53, 488.

Synthesis |

Catalysis |

Aromatic Compounds |

Aldehydes / Ketones

An undergraduate electroanalytical experimentJanata, JiriThis article presents a determination of vanillin and of other aromatic aldehyde can easily be accomplished by amperometric titration with a standard solution of 2,4-dinitrophenylhydazine.Janata, Jiri J. Chem. Educ.1976, 53, 399.

Illustrating gas chromatography and mass spectrometry. An undergraduate experimentGross, Michael L.; Olsen, Virgil K.; Forc, R. KenOne lab period is used to separate and collect the components of a ketone mixture; the second lab period is used to explain and demonstrate the MS instrumentation and the interpretation of ketone spectra; and in part three the spectra of the separated ketones are analyzed by individual students.Gross, Michael L.; Olsen, Virgil K.; Forc, R. Ken J. Chem. Educ.1975, 52, 535.

Gas Chromatography |

Mass Spectrometry |

Aldehydes / Ketones

The photoisomerization of cyclic ketones: An experiment in organic chemistryHaas, J. W., Jr.This experiment deals with parameters such as the nature of the excited state, effect of triplet quenchers on product formation, chemical structure and reaction rate and quantum yield when cyclopentanone and cyclohexanone are irradiated at 254nm. These cyclic ketones provide a variety of photolysis information in a short time span, are conveniently analyzed by gas chromatography, and are readily available at the requisite levels of purity.Haas, J. W., Jr. J. Chem. Educ.1974, 51, 346.

Stereochemistry of carbonyl addition reactionsGoller, Edwin J.This article is a brief summary of some of the more important unifying concepts that have been proposed in the study of the stereo chemistry of carbonyl addition reactions.Goller, Edwin J. J. Chem. Educ.1974, 51, 182.

Addition Reactions |

Stereochemistry |

Aldehydes / Ketones |

Aromatic Compounds

The significant role of chemical reactions in analytical chemistrySiggia, SidneyWith the increase in contemporary abilities to make measurements, the author has noticed a tendency to decrease the use of chemistry for analytical purposes. The author argues that chemists should still use the chemical expertise and lines of reasoning used by our chemistry predecessors and apply this extra degree of freedom to modern measuring approaches.Siggia, Sidney J. Chem. Educ.1974, 51, 98.

Recrystallization and melting point determinationKaye, Irving Allan; Yuska, HenryThis experiment is essentially an exercise in recrystallization and identification, by melting point and mixed melting point determination, an unknown ketone that has been transformed into either its 2,4-dinitrophenylhydrazone or semicarbazone derivative.Kaye, Irving Allan; Yuska, Henry J. Chem. Educ.1970, 47, 703.

Dipole moments: A physical-organic experimentRapp, Robert D.; Sturm, James E.The experiment described here applies dipole moment measurements to a study of the conformation of 2-chlorocyclohexanone.; students are required to estimate the dipole moment of the equatorial and axial conformers by a series of calculations.Rapp, Robert D.; Sturm, James E. J. Chem. Educ.1969, 46, 851.

Molecular Properties / Structure |

Conformational Analysis |

Aldehydes / Ketones

Photochemistry of organic compounds. II, Carbonyl compoundsSwenton, John S.Examines the electronics of the simple carbonyl group, the effect of structure on photoreduction of benzophenones and acetophenones, non-conjugated unsaturated ketones, the photochemistry of cyclic enones, and cross-conjugated cyclohexadienones.Swenton, John S. J. Chem. Educ.1969, 46, 217.

The formation of acetone from acetatesYoung, Jay A.; Taylor, John K.Suggests some research activities based on an article published previously in the Journal.Young, Jay A.; Taylor, John K. J. Chem. Educ.1962, 39, A962.

A separation and identification experiment for elementary organic chemistry laboratoryLaughton, Paul M.The student selects a test tube containing two unknowns and is told only that they have been selected from two of three possible groups: a primary or tertiary amine, an aldehyde or ketone, and an acid or phenol. The components are to be separated, their physical properties determined, their categories assigned, and one specific derivative prepared for each.Laughton, Paul M. J. Chem. Educ.1960, 37, 133.

Separation Science |

Qualitative Analysis |

Amines / Ammonium Compounds |

Aldehydes / Ketones |

Acids / Bases |

Phenols |

Physical Properties |

Synthesis

Relations between molecular structure and photodecomposition modesPitts, James N., Jr.It is now possible to predict qualitatively, and in some cases semiquantitatively, the extent of free radical processes versus direct molecular rearrangements in vapor-phase studies of the direct photolysis of aldehydes and ketones.Pitts, James N., Jr. J. Chem. Educ.1957, 34, 112.